4-N,4-N-bis(prop-2-enyl)benzene-1,4-diamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-nitro-N,N-di(prop-2-en-1-yl)aniline (12.22 g, 55.98 mmol) and tin (II) chloride dihydrate (64.45 g, 279.9 mmol) in EtOH (280 ml) was stirred and heated under reflux for 21 h. The cooled reaction mixture was concentrated under reduced pressure to a volume of 100 ml, and neutralised by the addition of 5 M NaOH. The precipitate was removed by filtration and the filtrate was extracted with EtOAc (4×200 ml). The combined organics were washed with brine (2×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was purified by chromatography (1:1 Hexane/EtOAc) to give the title compound (7.79 g, 74%) as a brown oil. heated under reflux for 21 h The cooled reaction mixture was concentrated under reduced pressure to a volume of 100 ml neutralised by the addition of 5 M NaOH The precipitate was removed by filtration the filtrate was extracted with EtOAc (4×200 ml) The combined organics were washed with brine (2×200 ml) dried (Na2SO4) The solvent was removed under reduced pressure to give a brown oil that was purified by chromatography (1:1 Hexane/EtOAc)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-nitro-N,N-di(prop-2-en-1-yl)aniline (12.22 g, 55.98 mmol) and tin (II) chloride dihydrate (64.45 g, 279.9 mmol) in EtOH (280 ml) was stirred and heated under reflux for 21 h. The cooled reaction mixture was concentrated under reduced pressure to a volume of 100 ml, and neutralised by the addition of 5 M NaOH. The precipitate was removed by filtration and the filtrate was extracted with EtOAc (4×200 ml). The combined organics were washed with brine (2×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was purified by chromatography (1:1 Hexane/EtOAc) to give the title compound (7.79 g, 74%) as a brown oil. heated under reflux for 21 h The cooled reaction mixture was concentrated under reduced pressure to a volume of 100 ml neutralised by the addition of 5 M NaOH The precipitate was removed by filtration the filtrate was extracted with EtOAc (4×200 ml) The combined organics were washed with brine (2×200 ml) dried (Na2SO4) The solvent was removed under reduced pressure to give a brown oil that was purified by chromatography (1:1 Hexane/EtOAc)